Inhibition of protein and lipid oxidation in liposomes by berry phenolics

The antioxidant activity of berry phenolics (at concentrations of 1.4, 4.2, and 8.4 mug of purified extracts/mL of liposome sample) such as anthocyanins, ellagitannins, and proanthocyanidins from raspberry (Rubus idaeus), bilberry (Vaccinium myrtillus), lingonberry (Vaccinium vitis-idaea), and black currant (Ribes nigrum) was investigated in a lactalbumin-liposome system. The extent of protein oxidation was measured by determining the loss of tryptophan fluorescence and formation of protein carbonyl compounds and that of lipid oxidation by conjugated diene hydroperoxides and hexanal analyses. The antioxidant protection toward lipid oxidation was best provided by lingonberry and bilberry phenolics followed by black currant and raspberry phenolics. Bilberry and raspberry phenolics exhibited the best overall antioxidant activity toward protein oxidation. Proanthocyanidins, especially the dimeric and trimeric forms, in lingonberries were among the most active phenolic constituents toward both lipid and protein oxidation. In bilberries and black currants, anthocyanins contributed the most to the antioxidant effect by inhibiting the formation of both hexanal and protein carbonyls. In raspberries, ellagitannins were responsible for the antioxidant activity. While the antioxidant effect of berry proanthocyanidins and anthocyanins was dose-dependent, ellagitannins appeared to be equally active at all concentrations. In conclusion, berries are rich in monomeric and polymeric phenolic compounds providing protection toward both lipid and protein oxidation.     

Berry phenolics and their antioxidant activity

Phenolic profiles of a total of 26 berry samples, together with 2 apple samples, were analyzed without hydrolysis of glycosides with HPLC. The phenolic contents among different berry genera varied considerably. Anthocyanins were the main phenolic constituents in bilberry, bog-whortleberry, and cranberry, but in cowberries, belonging also to the family Ericaceae genus Vaccinium, flavanols and procyanidins predominated. In the family Rosaceae genus Rubus (cloudberry and red raspberry), the main phenolics found were ellagitannins, and in genus Fragaria (strawberry), ellagitannins were the second largest group after anthocyanins. However, phenolic acids were dominant in rowanberries (genus Sorbus) and anthocyanins in chokeberry (genus Aronia). In the family Grossulariaceae genus Ribes (currants and gooseberry), anthocyanins predominated, as well as in crowberries (family Empetraceae genus Empetrum). In apples, hydroxycinnamic acids were the main phenolic subgroup. Extraction methods for berries and apples were studied to produce phenolic extracts with high antioxidant activity. Evaluation of antioxidant activity was performed by autoxidazing methyl linoleate (40 degrees C, in the dark). The extraction method affected remarkably both the phenolic composition and the antioxidant activity, but with statistical analysis the observed activity could not be well explained with the contents of individual phenolic subgroups.     

Identification and quantification of phenolic compounds in berries of Fragaria and Rubus species (family Rosaceae)

High-performance liquid chromatography combined with diode array and electrospray ionization mass spectrometric detection was used to study soluble and insoluble forms of phenolic compounds in strawberries, raspberries (red and yellow cultivated and red wild), arctic bramble, and cloudberries. Hydroxycinnamic acids were present as free forms in cloudberries and mainly as sugar esters in the other berries. Quercetin 3-glucuronide was the typical flavonol glycoside in all of the berries studied. The composition of the predominant anthocyanins can be used to distinguish the studied red Rubus species from each other since cyanidin was glycosylated typically with 3-sophorose (56%) in cultivated red raspberry, with 3-sophorose (30%) and 3-glucose (27%) in wild red raspberry, and with 3-rutinose (80%) in arctic bramble. Ellagic acid was present as free and glycosylated forms and as ellagitannins of varying degrees of polymerization. Comparable levels of ellagitannins were obtained by the analysis of soluble ellagitannins as gallic acid equivalents and by the analysis of ellagic acid equivalents released by acid hydrolysis of the extracts.     

Antioxidant activity in fruits and leaves of blackberry, raspberry, and strawberry varies with cultivar and developmental stage

Fruits and leaves from different cultivars of thornless blackberry (Rubus sp.), red raspberry (Rubus idaeus L.), black raspberry (Rubus occidentalis L.), and strawberry (Fragaria x ananassa D.) plants were analyzed for total antioxidant capacity (oxygen radical absorbance capacity, ORAC) and total phenolic content. In addition, fruits were analyzed for total anthocyanin content. Blackberries and strawberries had the highest ORAC values during the green stages, whereas red raspberries had the highest ORAC activity at the ripe stage. Total anthocyanin content increased with maturity for all three species of fruits. Compared with fruits, leaves were found to have higher ORAC values. In fruits, ORAC values ranged from 7.8 to 33.7 micromol of Trolox equivalents (TE)/g of fresh berries (35. 0-162.1 micromol of TE/g of dry matter), whereas in leaves, ORAC values ranged from 69.7 to 182.2 micromol of TE/g of fresh leaves (205.0-728.8 micromol of TE/g of dry matter). As the leaves become older, the ORAC values and total phenolic contents decreased. The results showed a linear correlation between total phenolic content and ORAC activity for fruits and leaves. For ripe berries, a linear relationship existed between ORAC values and anthocyanin content. Of the ripe fruits tested, on the basis of wet weight of fruit, cv. Jewel black raspberry and blackberries may be the richest source for antioxidants. On the basis of the dry weight of fruit, strawberries had the highest ORAC activity followed by black raspberries (cv. Jewel), blackberries, and red raspberries.     

Antioxidant activity and phenolic content of Oregon caneberries

Five types of caneberries [evergreen blackberries (Rubus laciniatus), marionberries (Rubus ursinus), boysenberries (Rubus ursinus x idaeus), red raspberries (Rubus idaeus), and black raspberries (Rubus occidentalis)] were analyzed for antioxidant activity by measuring their oxygen radical absorbance capacity (ORAC). In addition, the berries were analyzed for total phenolics, anthocyanins, procyanidins, and ellagic acid content. All of the berries had high ORAC activity ranging from 24 to 77.2 micromol of Trolox equiv/g of fresh berries. Anthocyanin content ranged from 0.65 to 5.89 mg/g, and phenolics ranged from 4.95 to 9.8 mg/g. Black raspberries had the highest ORAC and anthocyanin and phenolic contents. Only red raspberries had detectable amounts of procyanidin oligomers (monomer, dimers, and trimers). All berries had high levels of ellagic acid (47-90 mg/g), but boysenberries had the highest level prior to hydrolysis. The results from this study indicate that these caneberries were high in antioxidant activity and were rich sources of anthocyanins and phenolics.     

Plant phenolics affect oxidation of tryptophan

The effect of berry phenolics such as anthocyanins, ellagitannins, and proanthocyanidins from raspberry (Rubus idaeus), black currant (Ribes nigrum), and cranberry (Vaccinium oxycoccus) and byproducts of deoiling processes rich in phenolics such as rapeseed (Brassica rapa L.), camelina (Camelina sativa), and soy (Glycine max L.) as well as scots pine bark (Pinus sylvestris) was investigated in an H2O2-oxidized tryptophan (Trp) solution. The oxidation of Trp was analyzed with high-performance liquid chromatography using both fluorescence and diode array detection of Trp and its oxidation products. Mechanisms of antioxidative action of the phenolic compounds toward the oxidation of Trp were different as the pattern of Trp oxidation products varied with different phenolic compounds. The antioxidant protection toward oxidation of Trp was best provided with pine bark phenolics, black currant anthocyanins, and camelina meal phenolics as well as cranberry proanthocyanidins.     

Ellagitannins,flavonoids, and other phenolics in red raspberries and their contribution to antioxidant capacity and vasorelaxation properties

Analysis of extracts of Glen Ample raspberries (Rubus idaeus L.) by gradient, reverse phase HPLC with diode array and tandem mass spectrometry identified eleven anthocyanins, including cyanidin-3-sophoroside, cyanidin-3-(2(G)-glucosylrutinoside), cyanidin-3-glucoside, cyanidin-3-rutinoside, pelargonidin-3-sophoroside, pelargonidin-3-(2(G)-glucosylrutinoside), and pelargonidin-3-glucoside. Significant quantities of an ellagitannin, sanguiin H-6, with an M(r) of 1870 were detected along with lower levels of a second ellagitannin, lambertianin C, which has an M(r) of 2804. Other phenolic compounds that were detected included trace levels of ellagic acid and its sugar conjugates along with one kaempferol- and four quercetin-based flavonol conjugates. Fractionation by preparative HPLC revealed that sanguiin H-6 was a major contributor to the antioxidant capacity of raspberries together with vitamin C and the anthocyanins. Vasodilation activity was restricted to fractions containing lambertianin C and sanguiin H-6.     

Berry fruits: compositional elements, biochemical activities, and the impact of their intake on human health, performance, and disease

An overwhelming body of research has now firmly established that the dietary intake of berry fruits has a positive and profound impact on human health, performance, and disease. Berry fruits, which are commercially cultivated and commonly consumed in fresh and processed forms in North America, include blackberry ( Rubus spp.), black raspberry ( Rubus occidentalis), blueberry ( Vaccinium corymbosum), cranberry (i.e., the American cranberry, Vaccinium macrocarpon, distinct from the European cranberry, V. oxycoccus), red raspberry ( Rubus idaeus) and strawberry ( Fragaria x ananassa). Other berry fruits, which are lesser known but consumed in the traditional diets of North American tribal communities, include chokecherry ( Prunus virginiana), highbush cranberry ( Viburnum trilobum), serviceberry ( Amelanchier alnifolia), and silver buffaloberry ( Shepherdia argentea). In addition, berry fruits such as arctic bramble ( Rubus articus), bilberries ( Vaccinuim myrtillus; also known as bog whortleberries), black currant ( Ribes nigrum), boysenberries ( Rubus spp.), cloudberries ( Rubus chamaemorus), crowberries ( Empetrum nigrum, E. hermaphroditum), elderberries ( Sambucus spp.), gooseberry ( Ribes uva-crispa), lingonberries ( Vaccinium vitis-idaea), loganberry ( Rubus loganobaccus), marionberries ( Rubus spp.), Rowan berries ( Sorbus spp.), and sea buckthorn ( Hippophae rhamnoides), are also popularly consumed in other parts of the world. Recently, there has also been a surge in the consumption of exotic "berry-type" fruits such as the pomegranate ( Punica granatum), goji berries ( Lycium barbarum; also known as wolfberry), mangosteen ( Garcinia mangostana), the Brazilian a?aí berry ( Euterpe oleraceae), and the Chilean maqui berry ( Aristotelia chilensis). Given the wide consumption of berry fruits and their potential impact on human health and disease, conferences and symposia that target the latest scientific research (and, of equal importance, the dissemination of this information to the general public), on the chemistry and biological and physiological functions of these "superfoods" are necessary.     

Antioxidants in raspberry: on-line analysis links antioxidant activity to a diversity of individual metabolites

The presence of antioxidant compounds can be considered as a quality parameter for edible fruit. In this paper, we studied the antioxidant compounds in raspberry (Rubus idaeus) fruits by high-performance liquid chromatography (HPLC) coupled to an on-line postcolumn antioxidant detection system. Both developmental and genetic factors were assessed by comparing fruits from a single cultivar of different ripening stages and by comparing ripe fruits of 14 raspberry cultivars, respectively. The HPLC-separated antioxidant compounds were identified using HPLC-photodiode array coupled to mass spectrometry (quadrupole time-of-flight tandem mass spectrometry), using a reference lock mass for determining accurate masses. The dominant antioxidants could be classified as anthocyanins, ellagitannins, and proanthocyanidin-like tannins. During fruit ripening, some anthocyanins were newly produced, while others, like cyanidin-3-glucoside, were already present early in fruit development. The level of tannins, both ellagitannins and proanthocyanidin-like tannins, was reduced strongly during fruit ripening. Among the 14 cultivars, major differences (>20-fold) were observed in the levels of pelagonidin type anthocyanins and some proanthocyanidin type tannins. The content of ellagitannins varied approximately 3-fold. The findings presented here suggest that the content of individual health-promoting compounds varies significantly in raspberry, due to both developmental and genetic factors. This information will assist in the future development and identification of raspberry lines with enhanced health-promoting properties.     

Blackberry, black raspberry, blueberry, cranberry, red raspberry, and strawberry extracts inhibit growth and stimulate apoptosis of human cancer cells in vitro

Berry fruits are widely consumed in our diet and have attracted much attention due to their potential human health benefits. Berries contain a diverse range of phytochemicals with biological properties such as antioxidant, anticancer, anti-neurodegerative, and anti-inflammatory activities. In the current study, extracts of six popularly consumed berries--blackberry, black raspberry, blueberry, cranberry, red raspberry and strawberry--were evaluated for their phenolic constituents using high performance liquid chromatography with ultraviolet (HPLC-UV) and electrospray ionization mass spectrometry (LC-ESI-MS) detection. The major classes of berry phenolics were anthocyanins, flavonols, flavanols, ellagitannins, gallotannins, proanthocyanidins, and phenolic acids. The berry extracts were evaluated for their ability to inhibit the growth of human oral (KB, CAL-27), breast (MCF-7), colon (HT-29, HCT116), and prostate (LNCaP) tumor cell lines at concentrations ranging from 25 to 200 micro g/mL. With increasing concentration of berry extract, increasing inhibition of cell proliferation in all of the cell lines were observed, with different degrees of potency between cell lines. The berry extracts were also evaluated for their ability to stimulate apoptosis of the COX-2 expressing colon cancer cell line, HT-29. Black raspberry and strawberry extracts showed the most significant pro-apoptotic effects against this cell line. The data provided by the current study and from other laboratories warrants further investigation into the chemopreventive and chemotherapeutic effects of berries using in vivo models.     

Antioxidant activity of anthocyanins and their aglycons

The antioxidant activity of the six common anthocyanidins, pelargonidin, cyanidin, delphinidin, peonidin, petunidin, and malvidin, and their glycosidic forms was evaluated in three lipid-containing models [human low-density lipoprotein (LDL) and bulk and emulsified methyl linoleate]. In addition, the radical scavenging activity of the compounds against the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical was studied. Most anthocyanins and their aglycons acted as strong antioxidants in emulsion and LDL. Many compounds showed an activity comparable to the well-known antioxidants alpha-tocopherol, Trolox, catechin, and quercetin. In bulk methyl linoleate, anthocyanins and anthocyanidins possessed only a weak antioxidant activity or even oxidation-promoting activity. Depending on the anthocyanidin, different glycosylation patterns either enhanced or diminished the antioxidant power. For the most part, the activities of the glycosides and the aglycons did not differ remarkably in emulsion. In LDL the aglycons showed in general higher activities than the glycosides. In bulk oil, to the contrary, the glycosides were more effective than the aglycons.     

Concentration and mean degree of polymerization of Rubus ellagitannins evaluated by optimized acid methanolysis

Ellagitannins are a major class of phenolics largely responsible for the astringent and antioxidant properties of raspberries and blackberries. The Rubus ellagitannins constitute a complex mixture of monomeric and oligomeric tannins. Rubus oligomeric ellagitannins contain, beside the well-known ellagic acid and gallic acid moieties, the sanguisorboyl linking ester group. When exposed to acids or bases, ester bonds are hydrolyzed and the hexahydroxydiphenic acid spontaneously cyclizes into ellagic acid. This study describes a new, rapid procedure for the acid hydrolysis of Rubus ellagitannins in methanol, which results in maximal yield and enables the quantification of all the major reaction products. Additionally, the method provides the rationale for estimating the mean degree of polymerization of Rubus ellagitannins.     

Berry polyphenols inhibit α-amylase in vitro: identifying active components in rowanberry and raspberry

Polyphenol-rich extracts from a range of berries inhibited α-amylase in vitro, but the most effective were from raspberry and rowanberry (IC50 values of 21.0 and 4.5 μg/mL, respectively). The inhibitory components were examined by different approaches. Extracts from yellow and red raspberries were equally able to inhibit α-amylase. Because the yellow raspberry extracts effectively lacked anthocyanins, this suggested that they were not crucial for amylase inhibition. Notably, however, higher levels of other phenolic components in yellow raspberries (particularly, ellagitannins) did not increase amylase inhibition. Amylase inhibition in rowanberry was recovered in a fraction enriched in proanthocyanidins (PACs). Inhibition was ameliorated by bovine serum albumin, suggesting that PACs acted by binding to amylase. Co-incubation of rowanberry PACs with acarbose reduced the concentration of acarbose required for effective amylase inhibition. Such synergistic interactions could have implications for the current clinical use of acarbose for postprandial glycaemic control in type-2 diabetics.     

Cyanidin 3-rutinoside and cyanidin 3-xylosylrutinoside as primary phenolic antioxidants in black raspberry

Anthocyanin constituents in black raspberries (Rubus occidentalis L.) were investigated by HPLC-DAD, and their involvement as potent, significant antioxidants in black raspberries was demonstrated by three common antioxidant assays (FRAP, DPPH, ABTS) in this study. Five anthocyanins were present in black raspberries: cyanidin 3-sambubioside, cyanidin 3-glucoside, cyanidin 3-xylosylrutinoside, cyanidin 3-rutinoside, and pelargonidin 3-rutinoside. Their identities and structures, with particular emphasis on cyanidin 3-xylosylrutinoside, were confirmed by NMR spectroscopy. Two of these anthocyanins, cyanidin 3-rutinoside and cyanidin 3-xylosylrutinoside, predominated, comprising 24-40 and 49-58%, respectively, of the total anthocyanins in black raspberries. On the basis of both potency and concentration, cyanidin 3-rutinoside and cyanidin 3-xylosylrutinoside were found to be the significant contributors to the antioxidant systems of black raspberries. These findings indicate that these two anthocyanin compounds may function as the primary phenolic antioxidants in black raspberries. These two compounds exhibit potential biological activities that may be exploited in conjunction with other naturally occurring bioactive compounds in black raspberry fruit-based products used in clinical trials for the treatment of various types of cancer.     

Rubus fruit juices affect lipid peroxidation in a Drosophila melanogaster model in vivo

The antioxidant capacity of red cloudberry (Rubus chamaemorus) juice correlates well with its phenolic content. The red berries have a markedly higher content of anthocyanins, particularly cyanidin and pelargonidin derivatives, than that found in the more common yellow fruit. Conversely, the yellow juice has higher ellagitannin content. A feeding study was conducted to show the in vivo effects of the juices on lipid peroxidation in a sensitive Drosophila melanogaster stock. In young female flies there were significant (P < 0.01) effects of cloudberry juice on lipid peroxidation. In young male flies significant (P < 0.05) effects were found on primary products (hydroxyperoxides) with yellow juice and on secondary products (ketodienes) with red juice. With the red juice, a significant (P < 0.05) decrease in ketodienes was found in both young and old males. This study demonstrates that the effects of berry antioxidants on lipid peroxidation are easily and rapidly tested in vivo with the sensitive Drosophila model.     

Antioxidant activity and partitioning of phenolic acids in bulk and emulsified methyl linoleate.

To evaluate the effect of colloidal parameters on the activity of natural antioxidants, the effect of selected phenolic acids on both bulk and emulsified methyl linoleate oxidation (in the dark at 40 degrees C) was examined. Oxidation was monitored by determining the formation of hydroperoxides; their isomer distribution and ketodiene (oxodiene) products were monitored by using high-performance liquid chromatography. This study showed the system- and concentration-dependent antioxidant activity of phenolic acids. The scavenging of alpha,alpha-diphenyl-beta-picrazylhydrazyl radicals reflected the antioxidant activity in a bulk oil system but not in an emulsion. Specific interactions of the antioxidant with other compounds, for example, the emulsifier, and intramolecular hydrogen bonds may play an important role in reducing the antioxidant activity. Furthermore, these interactions of antioxidants with emulsifier have a strong influence on the partitioning of antioxidants. Thus, the proportion of the antioxidant solubilized in the lipid phase and particularly in the interface did not necessarily reflect the efficiency of the antioxidant.     

Preclinical evaluation of rapeseed, raspberry, and pine bark phenolics for health related effects

Rapeseed, raspberry, and pine bark are promising bioactive sources of plant phenolics selected from among ca. 100 previously screened plant materials for in vitro preclinical evaluation of health related effects. Phenolic extracts and isolated fractions of the selected materials were investigated for antioxidant, antimicrobial, antiinflammatory, and antimutagenic properties as well as for cell permeability. It was shown that rapeseed and pine bark phenolics and raspberry anthocyanins were good or excellent antioxidants toward oxidation of phosphatidylcholine membrane (liposomes), rapeseed oil (crude) phenolics were effective radical scavengers (DPPH test), and both raspberry and pine bark phenolics inhibited LDL oxidation. Rapeseed oil phenolics, principally vinylsyringol, raspberry anthocyanins, and pinoresinol and matairesinol, the principal components of pine bark phenolic isolate, were effective against formation of the proinflammatory mediator, prostaglandin E(2). Raspberry ellagitannins inhibited the growth of Proteus mirabilis and Klebsiella oxytoca. Pine bark and rapeseed had minor effects on the permeability of model drugs in Caco-2 experiments. None of the tested extracts were mutagenic nor toxic to Caco-2 cells or macrophages. Thus, phenolic isolates from rapeseed, raspberry, and pine bark and are safe and bioactive for possible food applications including functional foods intended for health benefit.     

Effect of processing and storage on the antioxidant ellagic acid derivatives and flavonoids of red raspberry (Rubus idaeus) jams

From red raspberries, ellagic acid, its 4-arabinoside, its 4' (4' '-acetyl) arabinoside, and its 4' (4' '-acetyl)xyloside, as well as quercetin and kaempferol 3-glucosides, were identified. In addition, two unidentified ellagic acid derivatives were detected. The free radical scavenging activity of the ellagic acid derivatives was evaluated by using the DPPH method and compared to that of Trolox. All of the isolated compounds showed antioxidant activity. The effect of processing to obtain jams on raspberry phenolics was evaluated. The flavonol content decreased slightly with processing and more markedly during storage of the jams. The ellagic acid derivatives, with the exception of ellagic acid itself, remained quite stable with processing and during 6 months of jam storage. The content of free ellagic acid increased 3-fold during the storage period. The initial content (10 mg/kg of fresh weight of raspberries) increased 2-fold with processing, and it continued increasing up to 35 mg/kg after 1 month of storage of the jam. Then a slight decrease was observed until 6 months of storage had elapsed. The increase observed in ellagic acid could be explained by a release of ellagic acid from ellagitannins with the thermal treatment.     

Antioxidant capacity, vitamin C, phenolics, and anthocyanins after fresh storage of small fruits.

Fresh strawberries (Fragaria x ananassa Duch.), raspberries (Rubus idaeus Michx.), highbush blueberries (Vaccinium corymbosum L.), and lowbush blueberries (Vaccinium angustifolium Aiton) were stored at 0, 10, 20, and 30 degrees C for up to 8 days to determine the effects of storage temperature on whole fruit antioxidant capacity (as measured by the oxygen radical absorbing capacity assay, Cao et al., Clin. Chem. 1995, 41, 1738-1744) and total phenolic, anthocyanin, and ascorbate content. The four fruit varied markedly in their total antioxidant capacity, and antioxidant capacity was strongly correlated with the content of total phenolics (0.83) and anthocyanins (0.90). The antioxidant capacity of the two blueberry species was about 3-fold higher than either strawberries or raspberries. However, there was an increase in the antioxidant capacity of strawberries and raspberries during storage at temperatures >0 degrees C, which was accompanied by increases in anthocyanins in strawberries and increases in anthocyanins and total phenolics in raspberries. Ascorbate content differed more than 5-fold among the four fruit species; on average, strawberries and raspberries had almost 4-times more ascorbate than highbush and lowbush blueberries. There were no ascorbate losses in strawberries or highbush blueberries during 8 days of storage at the various temperatures, but there were losses in the other two fruit species. Ascorbate made only a small contribution (0.4-9.4%) to the total antioxidant capacity of the fruit. The increase observed in antioxidant capacity through postharvest phenolic synthesis and metabolism suggested that commercially feasible technologies may be developed to enhance the health functionality of small fruit crops.     

Antioxidant activity of steryl ferulate extracts from rye and wheat bran

Antioxidant activity of steryl ferulates from other sources than rice have not yet been studied much, despite the fact that rice steryl ferulates (gamma-oryzanol) have been shown to possess good antioxidant activity. In this study, steryl ferulate extracts from wheat or rye bran were studied for their capability to inhibit hydroperoxide formation in bulk methyl linoleate and methyl linoleate emulsion. Further, their activity to scavenge DPPH radicals was analyzed. The activities were compared to synthetic steryl ferulates, rice steryl ferulates, ferulic acid, and alpha-tocopherol. Nonrice cereal extracts of steryl ferulates exhibited good antioxidant activity, especially in the bulk lipid system. The radical scavenging activity was similar to that of nonesterified ferulic acid, indicating that the ferulic acid moiety is responsible for the antioxidant properties. This study illustrates a new aspect to the health-promoting properties of rye and wheat.